Реакция #1726668

Уравнение реакции

water

chloroform

tetramethylammonium hydroxide

5-[4-(2-acetoxyethyl)-phenyl]dibenzothiophenium iodide

→

5-[4-(2-hydroxyethyl)phenyl]dibenzothiophenium iodide

Выход 84.0%

Растворители

methanol

Условия реакции

Обработка

1. 1
   Экстракцияto extract a chloroform layer
2. 2
   workup.DISTILLATIONAfter the solvent is distilled off under reduced pressure
3. 3
   Промывкаthe reaction product is washed with ethyl acetate

Методика

While cooling with ice, 10.0 g of dibenzothiophene-S-oxide synthesized in the above step (1) is added to 30 g of diphosphorus pentoxide/methanesulfonic acid (9/1), and further 10 ml of 2-phenylethyl acetate is added thereto. The reaction solution is stirred at room temperature for 6 hours, and then poured into ice water. The obtained aqueous solution is filtered, and 23 g of potassium iodide is added. Crystals precipitated are recovered by filtration to obtain 11.1 g of 5-[(4-(2-acetoxyethyl)-phenyl]dibenzothiophenium iodide. The obtained 11.1 g of 5-[4-(2-acetoxyethyl)-phenyl]dibenzothiophenium iodide is dissolved in 200 ml of methanol, 10.7 g of a 20% aqueous solution of tetramethylammonium hydroxide is added to the solution, followed by stirring at room temperature for 2 hours. Subsequently, 100 ml of ion exchange water and 100 ml of chloroform are added to the solution to extract a chloroform layer. After the solvent is distilled off under reduced pressure, the reaction product is washed with ethyl acetate to obtain 8.5 g of the aiming 5-[4-(2-hydroxyethyl)phenyl]dibenzothiophenium iodide.

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